Azamethiphos

Last updated
Azamethiphos
Azamethiphos structure.svg
Names
Preferred IUPAC name
S-[(6-Chloro-2-oxo[1,3]oxazolo[4,5-b]pyridin-3(2H)-yl)methyl] O,O-dimethyl phosphorothioate
Other names
Azamethifos; Azamethiophos
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard 100.047.827 OOjs UI icon edit-ltr-progressive.svg
PubChem CID
UNII
  • InChI=1S/C9H10ClN2O5PS/c1-15-18(14,16-2)19-5-12-8-7(17-9(12)13)3-6(10)4-11-8/h3-4H,5H2,1-2H3
    Key: VNKBTWQZTQIWDV-UHFFFAOYSA-N
  • InChI=1/C9H10ClN2O5PS/c1-15-18(14,16-2)19-5-12-8-7(17-9(12)13)3-6(10)4-11-8/h3-4H,5H2,1-2H3
    Key: VNKBTWQZTQIWDV-UHFFFAOYAD
  • O=P(OC)(OC)SCN1c2ncc(Cl)cc2OC1=O
Properties
C9H10ClN2O5PS
Molar mass 324.67 g·mol−1
Pharmacology
QP53AF17 ( WHO )
Legal status
  • AU: S6 (Poison)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Azamethiphos is an organothiophosphate insecticide. It is a veterinary drug used in Atlantic salmon fish farming along with other fish in the Salmonid family to control parasites, specifically sea lice. [1] [2] It is also used as an insecticide in biocidal products in Europe. [3]

Contents

Mode of action

Organophosphorus insecticides such as azamethiphos inhibit the action of the enzyme acetylcholinesterase. The acetylcholine, therefore, remains intact allowing the electrical signal to proceed without interruption. This phenomenon leads to overexcitation of the organism and eventually to the death of the insect. [4]

Azamethiphos penetrates through the cuticle or through the cuticle opening of the insect, and also acts by ingestion and absorption through the digestive system.

Registration

In Europe, azamethiphos is an active substance according to the Biocide Regulation 528/2012, to be used as insecticide.

It is used in several biocidal products in Europe, as insecticide mainly for professional users. It is commonly used against flies in animal housing.

Stability

Azamethiphos is sensitive to hydrolysis, especially at low pH.

Toxicity

Azamethiphos is of moderate acute oral toxicity with LD50 values ranging from 834 mg/kg in the rat to 1764 mg/kg in the hamster. Acute dermal toxicity is very low; LD50 values of >2020 and >6000 mg/kg are reported in the rabbit and an LD50 of >2150 mg/kg is reported in the rat.

Azamethiphos is an irritant to eyes and skin. It is considered toxic if inhaled and is harmful if swallowed. It is also believed to be a possible carcinogen and can cause damage to organs. [5]

Environmental toxicity

Azamethiphos is very toxic for the environment, with a LC50 on Daphnia magna of 0.33 μg/L. It is also considered to have a high acute oral toxicity for birds.

When azamethiphos is utilized as an insecticide in rainbow trout fish farming, it has been found that it causes changes in proteins within the fish. The proteins that have been altered are usually associated with the trout's clot formation, immune reaction, and free heme binding. Besides these changes, there has also been record of tissue damage in the fish. Other concerning results from studies show that there are changes in how the fish handle iron, with impacts such as iron accumulation in their organs and also possible chronic kidney trauma from deposits of iron in their body. [2] In addition to its negative impacts when used in fish farming, it has a poor impact on the environment after it is applied. While it does degrade relatively quickly in water, it is still able to spread in the aquatic environment and negatively impacts other species such as lobster larvae. [6]

Health effects due to exposure

Common exposure pathways for azamethiphos are dermal and ingestion. When exposed to low dosages of azamethiphos, common symptoms experienced are excessive salivation and eye-watering. Higher dosages of azamethiphos bring more severe symptoms, like severe nausea/vomiting, sweating, bradycardia, and convulsions. Muscle weakness is another likely symptom that can be experienced and can result in death if muscle weakness reaches the respiratory muscles. Some methods to prevent exposure to azamethiphos are wearing protective equipment and washing exposed skin before touching other surfaces.

Exposure to azamethiphos can affect women differently. Continued exposure to azamethiphos can cause reproductive effects regarding fertility, menstrual cycle disruptions, spontaneous abortions, stillbirths, and impaired fetal growth and development. [7]

Related Research Articles

A biocide is defined in the European legislation as a chemical substance or microorganism intended to destroy, deter, render harmless, or exert a controlling effect on any harmful organism. The US Environmental Protection Agency (EPA) uses a slightly different definition for biocides as "a diverse group of poisonous substances including preservatives, insecticides, disinfectants, and pesticides used for the control of organisms that are harmful to human or animal health or that cause damage to natural or manufactured products". When compared, the two definitions roughly imply the same, although the US EPA definition includes plant protection products and some veterinary medicines.

<span class="mw-page-title-main">Bifenthrin</span> Chemical compound

Bifenthrin is a pyrethroid insecticide. It is widely used against ant infestations.

<span class="mw-page-title-main">Imidacloprid</span> Chemical compound

Imidacloprid is a systemic insecticide belonging to a class of chemicals called the neonicotinoids which act on the central nervous system of insects. The chemical works by interfering with the transmission of stimuli in the insect nervous system. Specifically, it causes a blockage of the nicotinergic neuronal pathway. By blocking nicotinic acetylcholine receptors, imidacloprid prevents acetylcholine from transmitting impulses between nerves, resulting in the insect's paralysis and eventual death. It is effective on contact and via stomach action. Because imidacloprid binds much more strongly to insect neuron receptors than to mammal neuron receptors, this insecticide is more toxic to insects than to mammals.

<span class="mw-page-title-main">Chlorfenvinphos</span> Chemical compound

Chlorfenvinphos is an organophosphorus compound that was widely used as an insecticide and an acaricide. The molecule itself can be described as an enol ester derived from dichloroacetophenone and diethylphosphonic acid. Chlorfenvinphos has been included in many products since its first use in 1963. However, because of its toxic effect as a cholinesterase inhibitor it has been banned in several countries, including the United States and the European Union. Its use in the United States was cancelled in 1991.

<span class="mw-page-title-main">Ethion</span> Chemical compound

Ethion (C9H22O4P2S4) is an organophosphate insecticide. Ethion is known to affect a neural enzyme called acetylcholinesterase and prevent it from working.

<span class="mw-page-title-main">Nicotine poisoning</span> Medical condition

Nicotine poisoning describes the symptoms of the toxic effects of nicotine following ingestion, inhalation, or skin contact. Nicotine poisoning can potentially be deadly, though serious or fatal overdoses are rare. Historically, most cases of nicotine poisoning have been the result of use of nicotine as an insecticide. More recent cases of poisoning typically appear to be in the form of Green Tobacco Sickness, or due to unintended ingestion of tobacco or tobacco products or consumption of nicotine-containing plants.

<span class="mw-page-title-main">Fipronil</span> Chemical compound

Fipronil is a broad-spectrum insecticide that belongs to the phenylpyrazole chemical family. Fipronil disrupts the insect central nervous system by blocking the ligand-gated ion channel of the GABAA receptor and glutamate-gated chloride (GluCl) channels. This causes hyperexcitation of contaminated insects' nerves and muscles. Fipronil's specificity towards insects is believed to be due to its greater binding affinity for the GABAA receptors of insects than to those of mammals, and for its action on GluCl channels, which do not exist in mammals. As of 2017, there does not appear to be significant resistance among fleas to fipronil.

<span class="mw-page-title-main">Toxicity class</span> Pesticide classification system

Toxicity class refers to a classification system for pesticides that has been created by a national or international government-related or -sponsored organization. It addresses the acute toxicity of agents such as soil fumigants, fungicides, herbicides, insecticides, miticides, molluscicides, nematicides, or rodenticides.

<span class="mw-page-title-main">Phosmet</span> Organophosphate non-systemic insecticide

Phosmet is a phthalimide-derived, non-systemic, organophosphate insecticide used on plants and animals. It is mainly used on apple trees for control of codling moth, though it is also used on a wide range of fruit crops, ornamentals, and vines for the control of aphids, suckers, mites, and fruit flies.

<span class="mw-page-title-main">Benzotrichloride</span> Chemical compound

Benzotrichloride (BTC), also known as α,α,α-trichlorotoluene, phenyl chloroform or (trichloromethyl)benzene, is an organic compound with the formula C6H5CCl3. Benzotrichloride is an unstable, colorless or somewhat yellowish, viscous, chlorinated hydrocarbon with a penetrating odor. Benzotrichloride is used extensively as a chemical intermediate for products of various classes, i.e. dyes and antimicrobial agents.

<span class="mw-page-title-main">Sterigmatocystin</span> Chemical compound

Sterigmatocystin is a polyketide mycotoxin produced by certain species of Aspergillus. The toxin is naturally found in some cheeses.

<span class="mw-page-title-main">Spinosad</span> Medication

Spinosad is an insecticide based on chemical compounds found in the bacterial species Saccharopolyspora spinosa. The genus Saccharopolyspora was discovered in 1985 in isolates from crushed sugarcane. The bacteria produce yellowish-pink aerial hyphae, with bead-like chains of spores enclosed in a characteristic hairy sheath. This genus is defined as aerobic, Gram-positive, nonacid-fast actinomycetes with fragmenting substrate mycelium. S. spinosa was isolated from soil collected inside a nonoperational sugar mill rum still in the Virgin Islands. Spinosad is a mixture of chemical compounds in the spinosyn family that has a generalized structure consisting of a unique tetracyclic ring system attached to an amino sugar (D-forosamine) and a neutral sugar (tri-Ο-methyl-L-rhamnose). Spinosad is relatively nonpolar and not easily dissolved in water.

<span class="mw-page-title-main">Chlorethoxyfos</span> Chemical compound

Chlorethoxyfos is an organophosphate acetylcholinesterase inhibitor used as an insecticide. It is registered for the control of corn rootworms, wireworms, cutworms, seed corn maggot, white grubs and symphylans on corn. The insecticide is sold under the trade name Fortress by E.I. du Pont de Nemours & Company.

<span class="mw-page-title-main">Etofenprox</span> Chemical compound

Etofenprox is a pyrethroid derivative which is used as an insecticide. Mitsui Chemicals Agro Inc. is the main manufacturer of the chemical. It is also used as an ingredient in flea medication for cats and dogs.

<span class="mw-page-title-main">Acetamiprid</span> Chemical compound

Acetamiprid is an organic compound with the chemical formula C10H11ClN4. It is an odorless neonicotinoid insecticide produced under the trade names Assail, and Chipco by Aventis CropSciences. It is systemic and intended to control sucking insects (Thysanoptera, Hemiptera, mainly aphids) on crops such as leafy vegetables, citrus fruits, pome fruits, grapes, cotton, cole crops, and ornamental plants. It is also a key pesticide in commercial cherry farming due to its effectiveness against the larvae of the cherry fruit fly.

<span class="mw-page-title-main">Carbophenothion</span> Chemical compound

Carbophenothion also known as Stauffer R 1303 as for the manufacturer, Stauffer Chemical, is an organophosphorus chemical compound. It was used as a pesticide for citrus fruits under the name of Trithion. Carbophenothion was used as an insecticide and acaricide. Although not used anymore it is still a restricted use pesticide in the United States. The chemical is identified in the US as an extremely hazardous substance according to the Emergency Planning and Community Right-to-Know Act.

<span class="mw-page-title-main">Ethoprophos</span> Chemical compound

Ethoprophos (or ethoprop) is an organophosphate ester with the formula C8H19O2PS2. It is a clear yellow to colourless liquid that has a characteristic mercaptan-like odour. It is used as an insecticide and nematicide and it is an acetylcholinesterase inhibitor.

<span class="mw-page-title-main">EPN (insecticide)</span> Chemical compound

EPN is an insecticide of the phosphonothioate class. It is used against pests such as European corn borer, rice stem borer, bollworm, tobacco budworm, and boll weevil.

<span class="mw-page-title-main">Methyl isonicotinate</span> Chemical compound

Methyl isonicotinate is a toxic compound, which is used as a semiochemical. Other names for this compound are 4-pyridine carboxylic acid, and isonicotinic acid methyl ester. This compound is slightly toxic to the human body. It has an irritating effect on the eyes, skin, and respiratory tract. Moreover, the compound is used as the active ingredient in several sticky thrip traps to monitor and catch thrips in greenhouses.

References

  1. ↑ Azamethiphos Archived 2022-01-20 at the Wayback Machine , European Medicines Agency
  2. 1 2 Barisic, Josip; Cannon, Stuart; Quinn, Brian (November 7, 2019). "Cumulative impact of anti-sea lice treatment (azamethiphos) on health status of Rainbow trout (Oncorhynchus mykiss, Walbaum 1792) in aquaculture". Scientific Reports. 9 (1): 16217. Bibcode:2019NatSR...916217B. doi:10.1038/s41598-019-52636-1. PMC   6838116 . PMID   31700034.
  3. ↑ "Substance Information - ECHA". echa.europa.eu (in French). Retrieved 2023-02-13.
  4. ↑ Armosa factsheet on Azamethiphos, February 2022[ full citation needed ]
  5. ↑ "Azamethiphos: GHS-Classification". Pubchem .
  6. ↑ "Committee for Veterinary Medicinal Products: Azamethiphos Summary Report" (PDF). The European Agency for the Evaluation of Medicinal Products. 1999.
  7. ↑ "Azamethiphos". National Center for Biotechnology Information. 2024. Retrieved 14 March 2024.
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